Copper‐Promoted One‐Pot Trifluoromethylation of Aromatic Amines with Togni′s Reagent

Hong, Jianquan; Huo, Lianguang; Yang, Yupeng; Wang, Guifu; Zheng, Changge

doi:10.1002/slct.201700789

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Review Of Literature: Applications Of Sandmeyer Reaction1

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2024

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Cited by 8 publications

(1 citation statement)

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“…Hong et al . [ 60 ] examined the use of Togni’s reagent in one-pot Sandmeyer trifluoromethylation reaction. Their pathway started from the diazotization of the aromatic amines in the presence of HCl and t -BuONO.…”

Section: Review Of Literature: Applications Of Sandmeyer Reactionmentioning

confidence: 99%

Recent trends in the chemistry of Sandmeyer reaction: a review

et al. 2021

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Section: Review Of Literature: Applications Of Sandmeyer Reactionmentioning

confidence: 99%

Recent trends in the chemistry of Sandmeyer reaction: a review

et al. 2021

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Halogenation and Perfluoroalkylation Chemistry Using Hypervalent Halogen Compounds

Katayev

Jelier

Togni

2018

Patai's Chemistry of Functional Groups

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The introduction of halogenated functional groups by hypervalent iodine(III) reagents has proven to be a popular synthetic method in modern organic chemistry. Such diverse and often unique chemical behavior of iodine(III) compounds originates from their structural and bonding features. In this chapter, we aim to discuss the key structural properties, activation modes, and reactivity trends provided by λ 3 ‐iodane compounds as well as associated challenges therewith. Recent examples of chemo‐, regio‐, and stereoselective iodine(III)‐mediated halogenation and perfluoroalkylation reactions will be presented with an emphasis on contemporary fluorination and trifluoromethylation protocols.

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Site‐Specific Deaminative Trifluoromethylation of Aliphatic Primary Amines**

Xue,

Li,

Liu

et al. 2024

Angewandte Chemie

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The introduction of trifluoromethyl groups into organic molecules is of paramount importance in modern synthetic chemistry and medicinal chemistry. While methods for constructing C(sp2)‐CF3 bonds have been well established, the advancement of practical and comprehensive approaches for forming C(sp3)‐CF3 bonds remains considerably restricted. In this work, we describe an efficient and site‐specific deaminative trifluoromethylation reaction of aliphatic primary amines to afford the corresponding alkyl trifluoromethyl compounds. The reaction proceeds at room temperature with readily accessible N‐anomeric amide (Levin’s reagent) and bench‐stable bpyCu(CF3)3 (Grushin’s reagent) under blue light. The protocol features mild reaction conditions, good functional group tolerance, and moderate to good yields. Remarkably, the method can be applied to the direct, late‐stage trifluoromethylation of natural products and bioactive molecules. Experimental mechanistic studies were conducted, and a radical mechanism is proposed, wherein the dual roles of Grushin’s reagent have been elucidated.

show abstract

Copper‐Promoted One‐Pot Trifluoromethylation of Aromatic Amines with Togni′s Reagent

Cited by 8 publications

References 105 publications

Recent trends in the chemistry of Sandmeyer reaction: a review

Recent trends in the chemistry of Sandmeyer reaction: a review

Halogenation and Perfluoroalkylation Chemistry Using Hypervalent Halogen Compounds

Site‐Specific Deaminative Trifluoromethylation of Aliphatic Primary Amines**

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